Hydrocarbon product



Patent Aug. 1 1942 BYDBOOARBON PRODUCT deifrey H. ett, Craniord, N. 1.,i .L

Standard Oil Development Company, a corporation oi Delaware No Drawing.sApplieation'December 29, 1939,

e is,

I The present invention relates to an improvement in lubricants and aroils, as well as other hydrocarbon materials, es in respect toresistance to decomposition at elevated temperatures under on conditionssuch as are encountered in internal combustion es. The invention will befully unde w from the description which follows.

It has been found that mineral oil lubricants can be greatly improved ins t to their stability against decomposition, especially under heat andoxidizing conditions, by addition thereto of small amounts of certainsubstances. In the present case, a new group of substances hasdiscovered which are particularly efiective in re= ducing the oxidationof oils at elevated temperatures This group of substances comprises theperi-naphthothiazines and their derivatives, which may be defined by theformula in which R, R, and R" may be hydrogen, halogen, amino, mercapto,hydroxyl, or an organic group, such as am, aryl, -NH-alkyl, -NH-aryl,-N-alml, -N-aryl, -S-alkyi, -S-aryl, or an organic group containing aheterocyclic ring structure. There may be more than per 15 minuteintends ,1; 200 Q one such substituent-group attached to either hfollowing examples illustrate the value or both of the carbon rings.

The following are examples of this class of compounds:

Z-methyl-peri-naphtho-m-thiazine alkow, arony,

as ounce t amend oithe i No. 311,523

tions ranging from about 0.01% to about 1%, but the quantity generallyperierred is about 0.1%.

The addition agents of this invention do not have any detrimentaleflects on the physical character of the lubricating oil or the mineraloil to which they are added, such as viscosity, gravity and flash point.The present materials may be used as the sole blending agents, or theymay be added, in the case of a lubricant, with other ingredients whichserve other purposes. They are useful agents to be added to leaded oils,that is to say. lubricants containing lead oleate, lead naphthenate,lead sulionate or other heavy metal soaps. They also may be added alongwith oiliness agents, pour depressants, lubricating oil dyes, or agentsto give fluorescence. They may be used in conjunction with any otherantioxidants or with thickeners, sludg or sediment dispersers and thelike.

The value of the antioxidants of the present invention when used inlubricating oil blends has been determined by a standard oxygenabsorption test. This test isused for the most part in judging theomdation susceptibility of a lubricating oil at engine operationtemperatures. A known amount of omgen is bubbled through 10 cc. oi thelubricating oil maintained at 200 C.

The oxygen is continuously recycled. At the endof successive 15 minuteperiods, the amount or oxygen absorbed by the oil is measured. Theresults, usually termed the oxidation rate of the oil, are given as thenumber of cubic centimeters of oxygen absorbed by 10 cc. oi an oil ofthe new class of antioxidants in accordance with the present invention.

Example 1 ior its ondation rate as above, and the rates for threesuccessive 15 minute intervals were found to be 15, 2d and 31,respectively.

Example 3 oil descrl in pie 1 with approximately 0.2% of2-(m-hydroxyphenyl) -peri-naphtho-m-thiazine, an orange crystallinecompound, which may be prepared according to the method described inJour. Amer. Chem. Soc., 53:4056 (1931), was tested for its absorptionrate in the manner described, and the rates for four successive 15minute intervals were 14, 14, 18 and 20, respectively.

The present invention is not to be considered as limited by any of theherein described examples, which are given by way of illustration only,but is to be limited solely by the terms of the following claims inwhich it is desired to claim all novelty inherent in the invention.

I claim:

1. An improved lubricant comprising a mineral lubricating oil and asmall quantity of a compound of the formula:

. R in which R, R and R" are selected from the class consisting ofhydrogen and halogen atoms and amino, mercapto, hydroxyl and organicgroups.

2. An'improved lubricant comprising a mineral lubricating oil and asmall quantity of 2-methylperi-naphtho-m-thiazine.

3. An improved lubricant comprising a mineral lubricating oiland about0.1% of 2-methyl-perinaphtho-m-thiazine.

4. An improved lubricant for use at elevated temperatures comprising alubricating oil and about 0.01% to about 1.0% of a compound of theformula:

CR M in which R, R and R" are selected from the class consisting ofhydrogen and halogen atoms and amino, mercapto, hydroxyl and organicgroups.

5. An improved lubricant comprising a mineral lubricating oil and asmall quantity of Z-(m-hydroxyphenyl) -peri-naphtho-m-thiazine.

6. An improved lubricant comprising a mineral lubricating oil and about0.2% of Z-(m-hydroxyphenyl) -peri-naphtho-m-thiazine.

JEFFREY H. BARTLE'IT.

